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Winslow Homer painted many of his famous oceanscapes from a tiny studio on the rocky peninsula known as Prout's Neck, 12 miles south of Portland. Visitors today navigate a neighborhood of summer homes and a sprawling country-club property for a glimpse of the same dramatic coastline. Follow Highway 77 through South Portland (sometimes called "SoPo"), stopping off for bagels and coffee in
its hipper residential neighborhoods. In the affluent bedroom community of Cape Elizabeth, a detour along the two-lane Shore Road shows off the famed Portland Head Light lighthouse and quite a few stunning oceanfront homes.